a) Interpretation: The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, ethyl acrylate, is to be identified. Concept introduction: The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the product. To identify: The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated, ethyl acrylate, is hydrolyzed.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.11, Problem 19P

Interpretation Introduction

a)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, ethyl acrylate, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the product.

To identify:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated, ethyl acrylate, is hydrolyzed.

Interpretation Introduction

b)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acrolein is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor, acrolein, to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acroline.

Interpretation Introduction

c)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with an α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one.

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The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. Jo Han Sow La NaOH, THF O Nat H3O+ OH NaOH, THF The mechanism involves the following 5 steps: -ō cyclopropanone intermediate 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper, and then draw the structure of cyclopropanone intermediate 2 in the window. 1. NaOH, THF 2. H3O* OH

Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.11, Problem 19P

Interpretation Introduction

a)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, ethyl acrylate, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the product.

To identify:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated, ethyl acrylate, is hydrolyzed.

Interpretation Introduction

b)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acrolein is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor, acrolein, to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acroline.

Interpretation Introduction

c)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with an α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.11, Problem 19P

Interpretation Introduction

a)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, ethyl acrylate, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the product.

To identify:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated, ethyl acrylate, is hydrolyzed.

Interpretation Introduction

b)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acrolein is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor, acrolein, to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acroline.

Interpretation Introduction

c)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with an α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one.

Expert Solution & Answer

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 23.11, Problem 19P

Interpretation Introduction

a)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, ethyl acrylate, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the product.

To identify:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated, ethyl acrylate, is hydrolyzed.

Interpretation Introduction

b)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acrolein is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor, acrolein, to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acroline.

Interpretation Introduction

c)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with an α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one.

Expert Solution & Answer

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Answer 5

Chapter 23.11, Problem 19P

Interpretation Introduction

a)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, ethyl acrylate, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the product.

To identify:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated, ethyl acrylate, is hydrolyzed.

Interpretation Introduction

b)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acrolein is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor, acrolein, to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acroline.

Interpretation Introduction

c)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with an α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one.

Answer 6

Chapter 23.11, Problem 19P

Interpretation Introduction

a)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, ethyl acrylate, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the product.

To identify:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated, ethyl acrylate, is hydrolyzed.

Answer 7

Chapter 23.11, Problem 19P

Interpretation Introduction

a)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, ethyl acrylate, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the product.

To identify:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated, ethyl acrylate, is hydrolyzed.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acrolein is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor, acrolein, to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acroline.

Answer 9

Interpretation Introduction

b)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acrolein is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with α, β- unsaturated acceptor, acrolein, to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, acroline.

Answer 10

Interpretation Introduction

c)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with an α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one.

Answer 11

Interpretation Introduction

c)

Interpretation:

The product that will be produced when the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one, is to be identified.

Concept introduction:

The enamine obtained by reacting a ketone with cyclic amine reacts with an α, β- unsaturated acceptor to yield a substituted enamine as the intermediate which upon hydrolysis gives the products.

To identify:

The product that will be produced by the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with α, β- unsaturated acceptor, pent-3-ene-2-one.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 23.1 - Prob. 1P Ch. 23.1 - Prob. 2P Ch. 23.3 - Prob. 3P Ch. 23.3 - Prob. 4P Ch. 23.4 - Prob. 5P Ch. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7P Ch. 23.5 - Prob. 8P Ch. 23.6 - Prob. 9P Ch. 23.6 - What product would you Expect to obtain from base...

Solution Summary: The author explains the hydrolysis of the enamine obtained by reacting cyclopentanone and pyrrolidone with the unsaturated acceptor, ethyl acrylate.

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Chapter 23 Solutions